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Use of Dimethyldioxirane for the Oxidation of 1,2-Dithiolan-3-ones to 1-Oxides or 1,1-Dioxides. Preparation of 3H-1,2-Benzodithiol-3-one 1,1-Dioxide (Beaucage Sulfurizing Reagent)
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1999
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Derivative (Chemistry)BiochemistryNatural SciencesOrganic ChemistryDeoxygenationChemistryTwofold Molar ExcessQuantitative OxidationPharmacologyChemical DerivativeSynthetic ChemistryBeaucage Sulfurizing ReagentFourfold Molar Excess
Quantitative oxidation of 3H-1,2-benzodithiol-3-one to 3H-1,2-benzodithiol-3-one 1,1-dioxide (Beaucage sulfurizing reagent) is achieved by reaction of the dithiolanone with a fourfold molar excess of dimethyldioxirane for 2-4 hours at room temperature. A one- or twofold molar excess of reagent affords the 1-oxide as the main product.